Lithium Hydroxide → HCID 90031556, compound

HRID 531718Notes

Reaction equation

HRID 531718 reaction equation
Cl.FC1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=CC(C5CCNCC5)=CC=4)C=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)C=N1.[CH2:46]([N:53]1[CH:57]=[C:56]([C:58]2[C:66]3[C:61](=[N:62][CH:63]=[C:64]([C:67]4[CH:72]=[CH:71][C:70]([N:73]5[CH2:78][CH2:77][N:76]([CH2:79][C@@H:80]([OH:82])[CH3:81])[CH2:75][CH2:74]5)=[CH:69][CH:68]=4)[CH:65]=3)[N:60](S(C3C=CC(C)=CC=3)(=O)=O)[CH:59]=2)[CH:55]=[N:54]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[OH-].[Li+]>C1COCC1.CO.O>[CH2:46]([N:53]1[CH:57]=[C:56]([C:58]2[C:66]3[C:61](=[N:62][CH:63]=[C:64]([C:67]4[CH:68]=[CH:69][C:70]([N:73]5[CH2:74][CH2:75][N:76]([CH2:79][C@@H:80]([OH:82])[CH3:81])[CH2:77][CH2:78]5)=[CH:71][CH:72]=4)[CH:65]=3)[NH:60][CH:59]=2)[CH:55]=[N:54]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118524010HCID 118524010, compoundHCID 1185240853-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

Product 1

HCID 90031556HCID 90031556, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(4-(3-(1-benzyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)propan-2-ol (100 mg, 0.154 mmol) was hydrolyzed with lithium hydroxide (13 mg, 0.309 mmol) in THF/methanol/water (5./1/1 mL) to yield 31 mg (32.9% yield) of desired product. 1H NMR (CD3OD, 400 MHz): δ 8.605-8.601 (d, 1H), 8.537-8.533 (d, 1H), 8.22 (s, 1H), 7.95 (s, 1H), 7.75 (s, 1H), 7.69-7.67 (d, 2H), 7.38-7.29 (m, 5H), 7.17-7.15 (d, 2H), 5.42 (s, 2H), 4.29-4.25 (m, 1H), 4.00-3.80 (m, 2H), 3.35-3.20 (m, 2H), 3.35 (s, 2H), 3.25-3.20 (m, 2H), 3.19-3.10 (m, 2H), 1.30-1.27 (m, 3H). MS: m/z=493.2 (M+1), HPLC: 90.54% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-5c7629f1f9534185b27f833997827dbc
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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